You can visit both Tippling Rock and Ford's Folly in Sudbury in a day, or go for a more relaxed outing and limit yourself to one or the other. We – that would be me, Owen, Will and Teddy, for our first all-kids-present outing for this blog – did both. The whole hike follows part of the Bay Circuit Trail, a network of more than 200 miles of multi-use trails that encircles the Greater Boston area, through some 57 communities.

Tippling Rock offers a nice view toward Boston, after a fairly short and not-too-difficult walk. Ford's Folly is the fun-to-explore site of a dam Henry Ford built to supply water to Sudbury's historic Wayside Inn (unsuccessfully, as fate would have it).

Our hike began at the Tippling Rock trailhead off of the Boston Post Road (Route 20) on the edge of the Sudbury Conservation Commission's Weisblatt conservation property in Sudbury. We crossed into the Nobscot Boy Scout Reservation after a short while, and it only took about 25 minutes of relatively easy hiking and a bit less than a mile to get to the rock.

From there, we hiked across the Boy Scout Reservation to Ford's Folly. Around this time, we found ourselves, foolishly sans compass, in a welter of trails with intermittent signage to help us orient ourselves, so our detailed map could only do so much. Getting to the Folly should have taken three miles or so, but we definitely logged some extra distance trying to find the trail junctions we wanted. (We did pass an interesting landmark en route: an early 18th century burial ground for victims of smallpox...definitely worth a quick stop.)

We eventually made our way to the dam and spent some time walking over and around it, investigating the scrapped car on one side and also a very interesting compartment in the backside of the dam that housed part of its “works.” The geology hound in me was fascinated at the visible signs of mineral deposits forming from years of condensation on the stone dam, both in the “works” area and along the dam itself.

Heading back turned into more misguided wandering, although we did get to the top of Nobscot Hill and its fire tower, which we might have climbed had it not been thundering at the time.

Until this hike, I'd lived my entire hiking life without depending on a compass (perhaps due to unusually accurate guidebooks and maps), but those days are over. Not having one turned what should have been two to three pleasant hours and roughly six miles roundtrip into an all day, “when-will-we-be-done?” trek. As soon as we had a compass, thanks to an app for my phone we were luckily able to download, we were back on track and moving through the woods with confidence. Lesson learned.

With that said, even trips like these wind up logged in the family annals as shared memories. I was already laughing as I told a friend about our experiences on the way home, and I can just hear what the boys will tell their friends about being lost for HOURS and walking for MILES and all the BUGS. But most importantly, not one of them will ever leave home for a hike without a compass.

Planning your hike:

Parking: To reach Tippling Rock, we parked at the trailhead off Route 20 located at 641 Boston Post Road, just west of Horse Pond Road and about a quarter mile from Star Market. If you just want to visit Ford's Folly, park on Brimstone Lane, .8 miles south of Route 20.

The Bay Circuit Trail overlaps with a number of different trails, land owners, and terrain. In addition to the Bay Circuit Trail maps and guides, it is recommended that the maps of the area (as referenced in the trail descriptions for each section) be used to help with even more accurate navigation of the trail and its surrounding area.

There are no restrooms for most of the hike, though we did pass one outhouse on the Boy Scout property.

Water sources are unreliable; bring more than you think you'll need.

The aforementioned maps here are good, but the signage for the trails on the maps is a little sparse, so it's essential to have a compass and know how to use it.

Age recommendation: in optimal conditions, this should be fine for 6 and up. In heat or humidity, I'd recommend 10+.

Walking sticks/poles are useful for some of the hillier sections.

In warm weather, you will want a dependable mosquito/tick repellent, and if you're there long, tuck it in your pack to reapply as needed.

About the blogger: Melissa Macdonald is a featured guest blogger as part of AMC’s Kids Outdoors Boston Parent Ambassador program, which partners with local parents to share their outdoor experiences with this online community and beyond. Melissa lives west of Boston and enjoys exploring outdoors with her three boys: twin 10-year-olds and a six-year-old. Stay tuned throughout the summer for monthly blog posts and trip reports from Melissa, as well as from other local Parent Ambassadors and AMC’s Outdoors with Kids Boston author, Kim Foley MacKinnon.